Movies like The Dilemma (2011)
The best movies like The Dilemma (2011) are The Upside of Anger (2005), Young Adult (2011) and Please Give (2010). If The Dilemma hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedThe Sting (1973)8.0/10 from 3,177 votes
- NewestRedwood Diaries (2026)Released 2026
The Upside of Anger (2005)
After her husband runs off with his secretary, Terry Wolfmeyer is left to fend for herself -- and her four daughters. As she hits rock bottom, Terry finds a friend and drinking buddy in next-door neighbor Denny, a former baseball player. As the two grow closer, and her daughters increasingly rely on Denny, Terry starts to have reservations about where their relationship is headed.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisYoung Adult (2011)
A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisPlease Give (2010)
In New York City, a husband and wife butt heads with the granddaughters of the elderly woman who lives in the apartment the couple owns.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisThe Sting (1973)
A novice con man teams up with an acknowledged master to avenge the murder of a mutual friend by pulling off the ultimate big con and swindling a fortune from a big-time mobster.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Absolute CinemaMovies like thisCity Island (2009)
The Rizzos, a family who doesn't share their habits, aspirations, and careers with one another, find their delicate web of lies disturbed by the arrival of a young ex-con brought home by Vince, the patriarch of the family, who is a corrections officer in real life, and a hopeful actor in private.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisBenny & Joon (1993)
A mentally ill young woman finds love with an eccentric man who models himself after Buster Keaton.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisWho's Afraid of Virginia Woolf? (1966)
A history professor and his wife entertain a young couple who are new to the university's faculty. As the drinks flow, secrets come to light, and the middle-aged couple unload onto their guests the full force of the bitterness, dysfunction, and animosity that defines their marriage.
Why it matches: Recommended by TMDB viewers · both drama
Worth the HypeMovies like thisA Double Life (1947)
A Shakespearian actor starring as Othello opposite his wife finds the character's jealous rage taking over his mind off-stage.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisOut of Time (2003)
Matt Lee Whitlock, respected chief of police in small Banyan Key, Florida, must solve a vicious double homicide before he himself falls under suspicion. Matt Lee has to stay a few steps ahead of his own police force and everyone he's trusted in order to find out the truth.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisBlue Jasmine (2013)
After experiencing a traumatic misfortune, Jasmine French, a wealthy woman from New York, moves to San Francisco to live with her foster sister Ginger and the firm purpose of getting a new life, but she will be haunted by anxiety and memories of the past.
Why it matches: Recommended by TMDB viewers · both drama
Worth the HypeMovies like thisCreed III (2023)
After dominating the boxing world, Adonis Creed has thrived in his career and family life. When a childhood friend and former boxing prodigy, Damian Anderson, resurfaces after serving a long sentence in prison, he is eager to prove that he deserves his shot in the ring. The face-off between former friends is more than just a fight. To settle the score, Adonis must put his future on the line to battle Damian — a fighter with nothing to lose.
Why it matches: Recommended by TMDB viewers · both drama
Worth the HypeMovies like thisSleuth (2007)
Locked in a high-tech English manor, bound in a deadly duel of wits, Andrew Wyke and Milo Tindle come together as English gentlemen to discuss the matter of Wyke's wife: the woman both are sleeping with.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisThe Front Page (1974)
Ruthless Chicago newspaper editor Walter Burns resorts to dubious motives in order to get top reporter Hildy Johnson to cover one more big crime story before retirement.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisSwitching Channels (1988)
A television news chief courts his anchorwoman ex-wife with an eleventh-hour story.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisThe Gift (2015)
Simon and Robyn are a young married couple whose life is going as planned until a chance run-in with Simon's high school acquaintance sends their world into a tailspin.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisAntitrust (2001)
A computer programmer's dream job at a hot Portland-based firm turns nightmarish when he discovers his boss has a secret and ruthless means of dispatching anti-trust problems.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisThe Importance of Being Earnest (1952)
Two young gentlemen living in 1890s England use the same pseudonym ('Ernest') on the sly, which is fine until they both fall in love with women using that name, which leads to a comedy of mistaken identities.
Why it matches: Recommended by TMDB viewers · both comedy
Worth the HypeMovies like thisJulia (1977)
At the behest of an old and dear friend, playwright Lillian Hellman undertakes a dangerous mission to smuggle funds into Nazi Germany.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisKeeping Mum (2005)
A pastor preoccupied with writing the perfect sermon fails to realize that his wife is having an affair and his children are up to no good.
Why it matches: Recommended by TMDB viewers · both comedy
Popcorn FlickMovies like thisDeath of a Salesman (1985)
Willy Loman, an aging, failing salesman, struggles to accept reality and his failure to achieve the American Dream.
Why it matches: Recommended by TMDB viewers · both drama
Popcorn FlickMovies like thisRedwood Diaries (2026)
When strange entries begin appearing in her diary written in handwriting that isn't hers, new student Evie Quinn is pulled into a chilling mystery as the messages reveal secrets, predict impossible events, and point toward a truth someone has desperately tried to bury.
Why it matches: Similar story and style · both drama & comedy
Blonde Crazy (1931)
The adventures of a cocky con man and his beautiful accomplice.
Why it matches: Similar story and style · both drama & comedy
Worth the HypeMovies like thisLovers and Other Strangers (1970)
Mike Vecchio and Susan Henderson are preparing for their upcoming wedding. However, they seem to be the only two people at the wedding that are happy. Mike's brother Richie and his wife Joan are going through a divorce, which is upsetting his overly devout Catholic mother Beatrice. Also, Susan's father is carrying on an affair and her sex starved older sister Wilma is going through her troubles with her husband Johnny. All this is going on while Mike's best friend Jerry is trying to bed the maid of honor, Susan's cousin Brenda.
Why it matches: Similar story and style · both comedy & drama
¡Tango! (1933)
¡Tango! follows a formula established by Carlos Gardel with films such as Luces de Buenos Aires (The Lights of Buenos Aires, 1931) in which a melodramatic story is interspersed with tango songs. However, the film had less dialog and more music, making it more like a musical revue. This format would be copied by many subsequent films. The plot is derived from tango songs. Many of these songs tell of the seduction of an innocent slum girl by a rich man who promises her a glamorous life, but who abandons her when her looks fade. The stylized and sentimental plot of ¡Tango! revolves around a young man who is abandoned by his girlfriend for an older rich man and is heartbroken. The film follows his misfortunes.
Why it matches: Similar story and style · both drama
Anatomy of a Murder (1959)
Semi-retired Michigan lawyer Paul Biegler takes the case of Army Lt. Manion, who murdered a local innkeeper after his wife claimed that he raped her. Over the course of an extensive trial, Biegler parries with District Attorney Lodwick and out-of-town prosecutor Claude Dancer to set his client free, but his case rests on the victim's mysterious business partner, who's hiding a dark secret.
Why it matches: Similar story and style · both drama
Worth the HypeMovies like thisThree Can Play That Game (2007)
Shanté Smith has moved to Atlanta and become the Love Doctor, a relationship expert who uses her knowledge of the male psyche to help women get what they want.
Why it matches: Similar story and style · both comedy
The Shooting (1966)
Two miners agree to guide a mysterious woman, who has appeared in their camp from nowhere, to a nearby town; but soon, because of her erratic behavior, they begin to suspect that her true purpose is quite different.
Why it matches: Similar story and style · both drama
Popcorn FlickMovies like thisFiddler’s Green (2025)
At a rest stop bar in the middle of nowhere, a mysterious proprietor helps a guilt-ridden man reckon with his choices.
Why it matches: Similar story and style · both drama
Southside with You (2016)
Chronicles a single day in the summer of 1989 when the future president of the United States, Barack Obama, wooed his future First Lady on an epic first date across Chicago's South Side.
Why it matches: Similar story and style · both drama
SnoozefestMovies like thisLife Is a Wonderful Thing (2010)
A policeman who spies on the lives of others, an important banker married to a housewife who poses as a noblewoman. A precarious young masseuse and an electrician madly in love. Very different lives that end up intertwining. But also extremely complicated and troubled lives ... Even if, after all, life is a wonderful thing ...
Why it matches: Similar story and style · both comedy
SnoozefestMovies like this
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Frequently asked questions
What are the best movies like The Dilemma?
The closest matches to The Dilemma are The Upside of Anger (2005), Young Adult (2011) and Please Give (2010). Below are 27 more, each with the reason it matches.
What should I watch after The Dilemma?
Start with The Upside of Anger (2005), the closest match to The Dilemma.
What is the highest-rated movie like The Dilemma?
The Sting (1973), rated 8.0/10 by 3,177 TMDB users.
What is the newest movie like The Dilemma?
Redwood Diaries (2026) is the most recent release on this list.
Are there English movies like The Dilemma?
Yes: The Upside of Anger (2005), Young Adult (2011) and Please Give (2010).
How are movies similar to The Dilemma chosen?
First come films that Trakt’s viewers watch alongside The Dilemma, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.